[Synthesis of hetero-condensed quinazolones: 1,2,4-triazino[6,1-b]- and 1,2,5-triazino[2,3-b]quinazolones].
In the course of the systematic investigation of heterocondensed quinazolones derivatives of a new heterocyclic ring system, [1,2,5]triazepino[2,3-b]quinazolone have been developed as potential biologically active agents, which are new bioisoteric analogues of cholecystokinin antagonist diazepino[2,1-b]quinazolones. The authors worked out an original synthetic route for preparation of ring analogue [1,2,4]triazino[6,1-b]quinazolines from intermediates of the synthesis, too. Starting 2-alkyl-3-amino-quinazolones are easily prepared by reaction of 2-alkyl-benzoxazone with hydrazine hydrate. In the next step bromination reaction of the alpha-methylene group of 2-alkyl-substituents gave a mono-bromo derivative as major product. In the reaction of the bromo compound with N-nucleophyles 2-alkylamino-3-amino-quinazolones were obtained which reacted with alpha-halogeno-carbonyl compounds and led to the tricyclic quinazolones in ring closure reaction. The structural properties of the heterocyclic compounds were characterized by UV-VIS and NMR data and molecular modelling calculation.
Kiss
A
A
Semmelweis Orvostudományi Egyetem, Gyógyszerészi Kémiai Intézet, Budapest.
Almási
J
J
Szabó
M
M
Kökösi
J
J
Hermecz
I
I
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013053:Spectrophotometry; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry
C110495:1,2,4-triazino(6,1-b)quinazolone; C110496:1,2,5-triazepino(2,3-b)quinazolone; D001381:Azepines; D011799:Quinazolines; D014227:Triazines
Heterokondenzált kinazolonok szintézise: 1,2,4-triazino[6,1-b]- és 1,2,5-triazepino[2,3-b]kinazolonok elöállítása.